Cubs fans take to the streets to celebrate an end to 108 years of pain.
Photograph: Gorski/ ddp USA/ Barcroft Images

What an absolutely wonderful World Series we just watched. Close games, dominant pitching, spectacular plays; both teams boasting bright young stars (Bryant and Rizzo! Lindor and Ramirez!) buttressed by tested vets (Lester and Ross, Napoli and Crisp); the two best, most lovable managers in baseball (Maddon, Francona). And all the weight of all that history, all that futility – both franchises, defined by failure. One hundred and eight Sisyphean years had passed since the Cubs won the world championship. An almost-as-excruciating 68 for the Indians. Hollywood movies have been made about the haplessness of these teams. It could not have been scripted any better. This was a series any fan with a heart simply did not want to end.

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But end it did, with victory for the Cubs. And so we witnessed as the longest-suffering team and thousands of its famously loyal fans ripped off their hairshirts in a shower of champagne and beer and tears of joy. Conversely, of course, and this is less nice to think about, our deepest consolation goes to the losers. To get so close, once again, only to slip back down the mountain, a boulder-sized baseball bouncing off your head when you land at the bottom. What possible consolation could suffice?

Probably not an essay in the Guardian. But it’s all I can offer. It’s a story about me (because, like all writers, I am hopelessly self-absorbed) and being a sports fan, and how sports fans come to assume a self-identity that mirrors that of the teams they’ve chosen to root for. And how, really, this is not so good. But it’s also about how, really, in the end, everything is going to be fine. Or, at least, equally not-fine.

I am a 45-year-old Red Sox fan who grew up in New Jersey, Yankee territory. I was seven years old in 1978, when Bucky Dent hit a three-run homer off Mike Perez to win the one-game playoff that decided the final standings of the American League East that year. I was sitting – no, standing, we were all standing – in the very orange-and-tan TV room in the house of my parents’ friends, the Clairefields. I remember lots of screaming and shouting and emotion – Steve Clairefield was a Red Sox fan, as was my mother’s brother, Tom, who happened to be there with us – and learning about how the Yankees always won, and the Red Sox always lost. I learned about what had happened three years earlier in 1975, and about 1967 and 1948 and 1946, all the way back to 1918, the last time they won the world series, and then traded Babe Ruth, the greatest baseball player of all time, to the Yankees, cursing themselves with dark magic – they had not won again since, while the Yankees established themselves as the most dominant sports franchise of the century, winning 22 championships in 55 years.

I’m not sure whether I’d yet heard the story of David and Goliath. But it was this story, the history of the Red Sox, that solidified in my mind the heroic beauty of the underdog. I identified with it, deeply. Maybe it was because I was always small for my age, and not so good at sports. And many of my closest friends, for some reason, were generally older than I was. When I was five, I always played Tonto while Tom Linville, the nine-year-old son of my babysitter, got to be the Lone Ranger; I was always Robin to Batman, Hutch to Starsky, Kenickie to Zuko. Side-kick, second-fiddle, co-star. By choice: I knew my role, I embraced it. The Red Sox were the team for me.

There was a song that played on the radio all the time the following summer. “Have you heard about the lonesome loser? / Beaten by the Queen of hearts every time? / Have you heard about the lonesome loser? / He’s a loser but he still keeps on trying.” I remember hearing it in Chris Pack’s backyard, swinging a whiffle-ball bat with a handle wrapped in duct tape, loving it like a personal soundtrack.

That was me, a loser. A lovable one, I hoped. A scrappy underdog, like Tanner Boyle, the wise-ass shortstop from The Bad News Bears. I was happier that way. Or, at least, I told myself I was. Looking back, I see it as a psychological self-defense mechanism. It can be comforting, the warm blanket of loserdom. It’s an emotional bulwark against real pressure, against facing the real possibility that things can go one way or the other. Against risking the investment it takes to give a hundred percent effort and feel the full spectrum of feelings. Better, safer, to assume failure ahead of time.

I watched game six of the 1986 World Series in a roomful of my high-school-classmate Mets fans, outnumbered 20 to one, literally fighting (albeit playfully; drunken-15-year-old style) for my team. In the 10th inning, I stood on a couch, lording a two-run Red Sox lead over all of them, tasting the victory, feeling like a gladiator. “Are you not entertained?! You stupid Mets fans! Your team is only 24 years in existence, and you already have two world championships under your belt! This year it is my turn! I deserve this!”

Later that night, after riding my bike home alone, I lay facedown in my bed and cried.

But through all the pain, we come to love our identity, fans of losing sports teams. We tell ourselves the stories we want to hear. We are the noble downtrodden, sacrificing our own capacity for happiness because we love the sport itself so much. We are real fans, braving season after season of cold weather, out of love and devotion purer than that of other fans. “It is a far, far better thing that I do, by rooting for this team year after year, than I have ever done…” Anyone can be a Yankee fan. Being a Red Sox fan, or an Indians fan, or a Cubs fan, takes character. Only fans as loyal as we are have the guts to root for a perennially losing team, or a team with a reliable penchant for crumbling under pressure. I knew that the Red Sox would choke, again and again, and blow it at the end – usually to the Yankees. I was trapped by fate, sentenced by god to experience pain, and my experiencing that pain was a big part of who I was. Losing was a Boston Red Sox fan’s “essence,” a central element of the definition.

Until it wasn’t any more.

After the final out of the 2004 World Series, after a history-making bloody-sock miracle comeback over the Yankees, after an eighth straight victory had made the Red Sox baseball’s champions for the first time in the live-ball era, I sat in my apartment with my old friend Drew, a Sox fan from Massachusetts itself, and clinked a glass of whiskey. It was quiet. My wife, eight months pregnant, was asleep in the bedroom, the TV flickered on mute and we giggled, like punch-drunk eight-year-olds up past our bedtime at a sleepover. It was a strange new world, celebrating at the end of a baseball game. It was as if we’d walked through the wardrobe and ended up in Narnia.

Then Drew left and I padded around by myself for a while before going to bed in a discombobulated state of contemplativeness. What would it be like tomorrow, I wondered. In a world where the Red Sox can be champions? What kind of person would I be? Would I find myself feeling cheerful and happy all winter? With nothing to complain about? Next baseball season, next April, I was supposed to suddenly become optimistic? Repeat that sentence to yourself in a heavy Boston accent to learn how unnatural it sounds to a Red Sox fan over the age of 15.

I lay in bed, staring at the ceiling this time, discombobulated. In a sense, once the Red Sox had finally won, I didn’t know who I was any more. Losing was the Red Sox’s most definitive, most distinctive feature – and by extension, in baseball-fan terms, my own. Suddenly, I was just like everybody else.

One of the stranger pangs of sadness I have ever felt swelled in my chest. I knew that watching baseball would never be quite the same again. And I realized that true happiness – at least this kind, this kind that I’d been dreaming of for 26 years – is beyond my capacity to feel.

So it is in this counterintuitive light that I welcome Cubs fans to the new new Loser’s Society – we are such bad losers, we can’t even consider ourselves special for being a loser any more. We have lost everything. Now we have even lost loss.

And in turn, congratulations to fans of theCleveland Indians for being the real winners today. You can win for losing, it turns out. Because as weird as it may sound, sometimes a crown of thorns is the only thing that’s keeping the top of your head from falling off.